Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH3:12])[C:6](=[O:13])[C:5]2([CH3:15])[CH3:14].[CH3:16][N:17]1[C:21]([C:22]#[N:23])=[CH:20][CH:19]=[C:18]1B(O)O.[F-].[K+]>O1CCOCC1.CCOC(C)=O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[F:11][C:9]1[CH:10]=[C:2]([C:18]2[N:17]([CH3:16])[C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[CH:3]=[C:4]2[C:8]=1[N:7]([CH3:12])[C:6](=[O:13])[C:5]2([CH3:15])[CH3:14]
5-Bromo-7-fluoro-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one (0.10 g, 0.36 mmol), 1-methyl-5-cyano-2-pyrroleboronic acid (95 mg, 0.63 mmol), KF (69 mg, 1.19 mmol) were suspended in 1 mL of dioxane. Pd2(dba)3 monochloroform adduct (3.1 mg, 0.003 mmol) and Pd(P(t-Bu)3)2 (4.6 mg, 0.009 mmol) were added and the mixture was stirred vigorously at 45° C. for 6 h. The mixture was diluted with 100 mL of EtOAc and filtered through a plug of silica gel and concentrated. Purification by flash chromatography (2% acetone/hexane) afforded the title compound (30 mg, 28%) as a tan solid.
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